2-Chlorobenzaldehyde → HCID 23072928, compound

HRID 133692Notes

Reaction equation

HRID 133692 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH:10]([O:13][C:14]1[CH:15]=[C:16]([CH:28]=[C:29]([NH2:31])[CH:30]=1)[C:17]([NH:19][C:20]1[S:21][C:22]([C:25]([OH:27])=[O:26])=[CH:23][N:24]=1)=[O:18])([CH3:12])[CH3:11].C([BH3-])#N.[Na+]>CO>[CH:10]([O:13][C:14]1[CH:15]=[C:16]([CH:28]=[C:29]([NH:31][CH2:4][C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=2[Cl:1])[CH:30]=1)[C:17]([NH:19][C:20]1[S:21][C:22]([C:25]([OH:27])=[O:26])=[CH:23][N:24]=1)=[O:18])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 69962-ChlorobenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 23072922HCID 23072922, compound

Product 1

HCID 23072928HCID 23072928, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Chlorobenzaldehyde (0.012 ml, 0.11 mM) was added to 2-[(3-isopropoxy-5-aminobenzoyl)amino]-5-thiazolecarboxylic acid (29 mg 0.09 mM) and 4A molecular sieves (90 mg) in methanol under an inert atmosphere at room temperature. After 1 hr sodium cyanoborohydride (7 mg, 0.11 mM) was added and the reaction mixture stirred for 16 hrs. The reaction mixture was filtered, concentrated in vacuo, the residue stirred with water then extracted with ethyl acetate (3×10 ml). The organic extracts were washed with brine (20 ml), dried (MgSO4), filtered and concentrated in vacuo to give the title compound as a pale yellow solid (22 mg, 55%); 1H nmr (d6-DMSO, δ values): 1.22 (6H, d); 4.36 (2H, m); 4.58 (1H, m); 6.24 (1H, s); 6.47 (1H, m); 6.84 (2H, m); 7.26 (3H, m); 7.37 (2H, m); 7.45 (1H, m); 7.76 (1H, br s). MS [M-CO2H]−400, 402.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. stirringthe residue stirred with water
  4. extractionthen extracted with ethyl acetate (3×10 ml)
  5. washThe organic extracts were washed with brine (20 ml)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bf7d9c346574474c8fdf74852798787f
Source dataset
uspto-grants-2008_06
Patent number
US07390908B2

Reaction notes

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